DEAR JACK,
Rest is difficult when I dream of the past behind.
Unless you know how to stop the darkness ahead.
Not until then will I stop thinking of the dead.

❂

𝙨𝙤𝙣𝙜 𝙤𝙛 𝙘𝙝𝙤𝙞𝙘𝙚—
𝙮𝙤𝙪'𝙫𝙚 𝙜𝙤𝙩 𝙖 𝙛𝙧𝙞𝙚𝙣𝙙 𝙞𝙣 𝙢𝙚
𝙨𝙡𝙚𝙚𝙥𝙞𝙣𝙜 𝙖𝙩 𝙡𝙖𝙨𝙩

❂

THERE WAS NOTHING ROSE WOULDN'T DO TO FIND JACK. He had been missing on a cold night and all she had wanted was to sit in a motel room with him, watch TV and forget about the cruel world around them. He was a perfect distraction even if he had often felt more like a job.

Pulling her jacket tightly around her, cold breaths of air had escaped her lips from the freezing air. She remember how important Jack was to Kelly and how she had promised her that she would help Jack in the world he would be born into. Even if she had expected a newborn to be her newest job, having Jack older and able to hold himself together was much better. It was easier to connect with him and in a way, made her feel like there was a chance she'd have a friend. And having a friend in a line of work that involved killing monster was not as easy as one would hope.

Sitting alone in a dark alleyway, Jack had tried desperately to hold on to the memories of his mother. It was all he had left of her after all. He wished she was here tonight. Kelly would've made sure to take him somewhere safe and feel like home. But tonight, he had felt anything but.

Hearing sound of her footsteps approaching him, Jack glanced up at Rose making her way towards him. If he hadn't felt so alone, he would've smiled. Already it had been the Winchester brothers once again falling behind and Rose first to find him. She had been there yet again when he had wanted someone to tell him it would all be okay.

There wasn't anything Rose felt that she could say that would make Jack feel better. She had been in his place before. Dean had hated her, seeing nothing but evil and wanted her gone forever. And there was Sam Winchester, standing for what he believed in— and that was her.

"Everyone's looking for you." Roses voice had been  soft as she spoke her words carefully. "I thought you'd leave for good."

Her words had made Jack feel worse. Not because he was crushed the same way Dean had hurt him, but because he had hurt her and that made him mad at himself. "I couldn't sit there. I made everyone mad. I keep screwing up."

"You don't screw up. What's happening with all of us, it's hard, but it's not your fault. I just don't know if I can handle you disappearing on me again."

A small smile had came to Jack's lips but he couldn't meet her eyes just yet. He was feeling the guilt for leaving, but he did remember that she was the one who had searched for him just like before. "You always find me."

A laugh had bubbled out as she shrugged her shoulders. "Guess I'm tethered to you." A wave of pain had hit her seconds later as her smile had dropped. "Jack, you can't always count on me to be there. I screw up and it's only a matter of time before I screw up and you get the short end of the stick."

"Would you do it on purpose?" His question had earned a shake of the head as her response. "Then I cant be mad at you."

She had looked him over curiously. Someone who was considered so dangerous was one of the nicest people she had ever met. "I can't ever be mad at you either," she said softly. Giving him a small nudge, she had caused him to break out into a small grin. "We can be friends, I guess. You know, if you want."

This had been his chance he was looking for. All Jack could think about was how proud his mom would be for seeing him making a friend so soon. It wasn't just anyone either, it had been someone he knew that his mom had liked. In Kelly's eyes, Rose was a misguided girl that even with her issues was kind at heart.

"I'd like that."

Unable to keep it in any longer, Rose dug her hand into her pocket before tossing something right into Jack's lap. Suspicious of what it was, he pinched a key between his fingers as he held it up.

"Figured if we're gonna be friends, we could start off by getting out of that crap room and have our own."

"Dean will get mad."

"Oh, who cares?" she laughed. "Think about it. No Dean yelling at us, no Sam telling us to go to bed. Just us, some TV and since we're out here... Maybe we can hit up a gas station, grab some snacks. Make the most of this."

Jack was weary of her suggestion. Though it had sounded like a great way to spend the time, he did not want to upset the Winchesters so early. Then he looked to Rose just before he handed the key back with his rejection. It had been the first time since they had met that there was no pain hidden behind her eyes. She was filled purely with excitement and he had known that was something he wanted to be a part of. "What kind of snacks?"

Jack's question had been enough for Rose to jump up to her feet. Extending her hand out, she waited for him to grasp on and help him to his feet beside her. This excitement had not just been from the thought of finding peace in a motel room, but because Jack had been there to enjoy it with her. It was a breath of fresh air that she had needed since that night.

❂

JACK AND ROSE HAD MADE THE MOST OF THE NIGHT TOGETHER. There was enough laughter that kept Dean Winchester with his ear pressed to the door and a scowl on his face most of the night. Sam had felt relieved that after what they had been through, there had been a way to find the good in the world they lived in. It allowed him to sleep easy and forget just for the moment.

In the morning, Rose had woken groggy and exhausted. If she had listened to Sam's instructions not to stay up late, there would not have been an issue and she knew that when she had saw him it would be clear what he would say. I told you so!

Jack had still been fast asleep. He had gotten less sleep than Rose had but he would never tell her that. Having a bed to sleep in and end the night off with a friend, he should've been able to sleep peacefully. Instead, he had felt her tossing and turning beside him as she had dealt with her trauma in her sleep. Just the other day her family had been torn away from her. Family that was blood. And there was nothing that would bring them back.

Eventually he had found his eyes closing before the sun could come up. Now he swore he could sleep until the sun went down. He didn't even bother waking to Rose tossing his arm off her and her leaving him all to himself.

Rose had rubbed her eyes as a yawn had escaped from her when she walked into the Winchester brothers room. "Morning, Sam," she mumbled.

He chuckled in response as he shook his head. "Told you so." Setting his tablet down as she sat across from him, he couldn't help but smile at her. "How'd last night go?"

"Good. Bet your night went well too? Donatello and Dean... sounds like nothing but fun here."

Scoffing, Sam couldn't help but roll his eyes. "Yeah, sure. Donatello got his own room but Dean..."

"Was Dean?"

"Exactly." Leaning back in his chair, he let out a yawn of his own to show his exhaustion. "So, how about it? You stay up all night watching cartoons?"

"Yeah, guess so."

"Well deserved. Almost had to come in myself and watch."

"We watched Scooby Doo," she laughed. Scooby Doo was not exactly Sam's favorite thing to watch. He didn't see the appeal of it, it was just something on TV that played the part of background noise while they crashed at motels. He chose to not admit it, but it started to become a comfort noise. As long as that was on, the two he rode with, they were going to be okay.

Throwing open the motel doors all the way, Dean couldn't wait to share his piece. "Is that what we're calling it now?"

"Dean," Rose drawled on in annoyance. This was the moment that Sam had prepared for but still, when it came, he felt anything but ready to help defend Rose on her choice to get a room with Jack.

"Nope," Dean said quickly before he could hear an excuse. Nothing she could say was going to change his thoughts. "You two are not allowed alone together. No way. I'm not dealing with a child that what... daughter of Crowley and son of Lucifer... Not a great combo. I will not be a babysitter to that kinda kid. Hell raiser."

"Not funny," Rose grumbled, grabbing her food from him.

"So you're telling me nothing happened last night besides Scooby Doo?" His question had been filled with disbelief that only frustrated her further.

"Get the pregnancy test, Dean. I'll pee if thats what you want," Rose snapped.

The door had opened once more and in walked in Donatello with a smile. "Hey, guys. Got a minute to talk about Jack?" Donatello asked, catching sight of the food. Sneaking a hand towards Roses food, it was to his luck to have it swatted away.

"Uh, but we just talked about Jack," Sam said in confusion. "You were just here."

Laughing uncomfortably, he looked to Rose and Dean as if they would let him in on a joke. "No, I wasn't. I was grabbing breakfast burritos. Extra spicy." Lifting up the bag in his hand, he had shown all the proof he needed to show he wasn't crazy.

Wide eyed in concern, Sam had looked to the two. There was no need to exchange words as they knew that something was up against them again. Choosing to leave their breakfast behind to take on what was next to come, the three made quick work of heading out. Donatello had a brief moment of complications. Letting out a huff, he turned back towards the table, grabbing some of the extra food before finally following along.

❂

DONATELLO HAD PUT HIMSELF TO USE. The entire car ride, his eyes had been squeezed shut as he attempted to feel where Jack's wave of power could have gone. It hadn't taken Sam Winchester long to figure out that whoever had taken Jack, was leading him to what was known as a gate of Hell in Jasper, Wyoming.

The Impala had came to a halt that had caused Jack and the one impersonating the prophet to both stop in confusion and worry. For a moment, Jack had broken his concentration from opening a portal to Hell. The rift he had created in the Earth below his feet had slowly began to close before the impersonator had demanded for Jack to continue.

Startled, Jack was unsure who he should listen to. On one end, someone that Rose had said had a direct line to God, his grandfather, told him to do it while across the way had stood the Winchesters and that very same man.

For Dean, there was no reason to sit back and wait for Jack to call the decision. He yanked his gun out, firing several rounds into the impersonator without much thought. If they were using Jack to open up a gate to Hell, there was no reason to ask questions before shooting.

The bullets that lodged themselves into the impersonator had done their job as with a whip of smoke, a man dressed in a white suit had stood beside Jack now. Bothered that the Winchesters were as quick to act as he had heard rumored around Hell, he snapped his fingers lazily.

It had been instant when the four standing beside the Impala had felt the air ripped from their lungs. At first it had felt as if they were drowning, no way of escaping the immense pain and find the relief through a single breath of air. Once they had all fallen to their knees in agonizing pain, it was as if their lungs were on fire. All had their hands wrapped tightly around their throats, hoping by some miracle, clawing would make it all disappear.

Jack's attention on Asmodeus had not stayed for long. The people that had saved him had been struggling to live for another moment which only confirmed that the man beside him was not to be trusted. "You're hurting my friends!" The anger inside him had risen as his breath had began to pick up. Jack's eyes had glowed bright with gold that were beautiful if you were not on the wrong side of them. As for Asmodeus, he was scared and could no longer stand his ground. With a whip in the air, he hs vanished from his spot.

No longer seeing the evil beside him, Jack took a step back as his eyes had shifted back to their usual blue. As for the four that were on their hands and knees, they had begun to gasp for breath when Asmodeus's magic had been lifted and they could finally feel again.

Once more on this long journey that the Winchester's had been put on, they were faced with another yellow eyed demon. After dealing with Azazel and Ramiel, they could only hope that Asmodeus was someone that wouldn't stand in their way much longer.